Methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate, having the formula ##STR1## also defined as methyl .alpha.-cyclogeranate is a known compound [see e.g. Helv. Chim. Acta 42, 2597 (1959)]. Up to now, however, its olfactive properties have remained unrecognized in the art.
Among the great variety of synthetic compounds presently at the disposal of perfumers, there appears to be several alicyclic ester derivatives analogous or homologous to compound (I). Said ester derivatives are summarized hereinafter.
______________________________________ Alicyclic esters Odour description Reference ______________________________________ ##STR2## no odour decsription Helv. Chim. Acta 42,2597 (1959) ##STR3## camphoraceous, woody, flat, medi- cinal side-note U.S. Pat. No. 4,113,663 ##STR4## refreshing, oily- green, vegetable, apple-like Arctander.sup.(1) (1198) ##STR5## diffusive rose note, honey, spicy, fruity, berry-like U.S. Pat. No. 4,113,663 ##STR6## slightly fruity and tobacco-like notes, eucalyptus U.S. Pat. No. 4 006 108 ##STR7## general fruity, but not apple-like U.S. Pat. No. 4 144 199 + .alpha. and .gamma.-isomers ______________________________________ .sup.(1) S. Arctander, Perfume and Flavor Chemicals, Montclair N.J. 1969 (section no.)
From the above discussed state of the art one can deduct that higher homologues of methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate (I) are the only compounds presenting an interest for the perfumery. These higher homologues are more specifically ethyl ester derivatives having an ethyl group at position 2 of the six membered ring, as well as compounds possessing an additional methyl group at position 3, and isomeric mixtures of corresponding doubly unsaturated derivatives, ethyl .alpha.-, .beta.- and .gamma.-safranates more precisely.
Lower homologues such as methyl .beta.-cyclogeranate and compound (I), however, never retained the perfumer's attention.
In contradiction with the above, we have surprisingly found that methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate (I) presented a great interest for the perfumery and that it could advantageously be used as perfuming ingredient.